Diketopyrrolopyrrole-based (DPP-based) polymers are a very important class of materials for both organic solar cells (OSCs) and organic field-effect transistors (OFETs). Here we report an optimised synthesis of fluorinated dithienyl-diketopyrrolopyrrole (fDT-DPP) and three new highly fluorinated fDT-DPP-based materials obtained from direct heteroarylation polymerization (DHAP). This study confirms the properties of the fluorine atom in a polymer, activation of the α-position hydrogen on thiophene moieties, decreasing HOMO and LUMO energy, lower bandgaps and modification of the solubility and morphology of the materials.